Organometallic compound and organic light-emitting device including the same

ABSTRACT

An organometallic compound represented by Formula 1: 
     
       
         
         
             
             
         
       
         
         
           
             wherein in Formula 1, CY 1 , R 1  to R 3 , R 11  to R 13 , R 21 , and b1 are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2015-0035156, filed on Mar. 13, 2015, in the KoreanIntellectual Property Office, the content of which is incorporatedherein in its entirety by reference.

BACKGROUND

1. Field

One or more embodiments relate to an organometallic compound and anorganic light-emitting device including the same.

2. Description of the Related Art

Organic light emitting devices (OLEDs) are self-emission devices thathave wide viewing angles, high contrast ratios, and short responsetimes. In addition, the OLEDs have good brightness, driving voltage, andresponse speed characteristics, and produce full-color images.

A typical an organic light-emitting device includes an anode, a cathode,and an organic layer that is disposed between the anode and the cathode,wherein the organic layer includes an emission layer. A hole transportregion may be disposed between the anode and the emission layer, and anelectron transport region may be disposed between the emission layer andthe cathode. Holes provided from the anode may move toward the emissionlayer through the hole transport region, and electrons provided from thecathode may move toward the emission layer through the electrontransport region. The holes and the electrons are recombined in theemission layer to produce excitons. These excitons change from anexcited state to a ground state, thereby generating light.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

One or more embodiments relate to a novel organometallic compound and anorganic light-emitting device including the same.

According to an aspect, an organometallic compound represented byFormula 1 is provided:

wherein in Formula 1,

CY₁ is selected from a benzene ring and a naphthalene ring,

R₁ to R₃ are each independently selected from a hydrogen, a deuterium, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₂-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₂-C₆₀heteroarylthio group, a substituted or unsubstituted C₃-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₅₁)(Q₅₂)(Q₅₃),

R₁₁ to R₁₃ and R₂₁ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₂-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₂-C₆₀heteroarylthio group, a substituted or unsubstituted C₃-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group, —N(C)₁)(Q₂),—B(Q₃)(Q₄), and —P(═O)(Q₅)(Q₆),

when CY₁ is the benzene ring, b1 is an integer selected from 0 to 4,

when CY₁ is the naphthalene ring, b1 is an integer selected from 0 to 6,

at least one selected from R₁₁ to R₁₃ in Formula 1 is not a hydrogen,and

at least one of substituents of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₇-C₆₀ arylalkyl group,substituted C₁-C₆₀ heteroaryl group, substituted C₂-C₆₀ heteroaryloxygroup, substituted C₂-C₆₀ heteroarylthio group, substituted C₃-C₆₀heteroarylalkyl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group is selected from:

a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroarylgroup, a C₂-C₆₀ heteroaryloxy group, a C₂-C₆₀ heteroarylthio group, aC₃-C₆₀ heteroarylalkyl group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —N(Q₁₁)(Q₁₂), —B(Q₁₃)(Q₁₄), and —P(═O)(Q₁₅)(Q₁₆),

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ heteroaryloxygroup, a C₂-C₆₀ heteroarylthio group, a C₃-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ heteroaryloxygroup, a C₂-C₆₀ heteroarylthio group, a C₃-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀ heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₂₁)(Q₂₂), —B(Q₂₃)(Q₂₄), and —P(═O)(Q₂₅)(Q₂₆); and

—N(Q₃₁)(Q₃₂), —B(Q₃₃)(Q₃₄) and —P(═O)(Q₃₅)(Q₃₆);

wherein Q₁ to Q₆, Q₁₁ to Q₁₆, Q₂₁ to Q₂₆, Q₃₁ to Q₃₆ and Q₅₁ to Q₅₃ areeach independently selected from a hydrogen, a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted C₂-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₂-C₆₀ heteroarylthio group, a substituted orunsubstituted C₃-C₆₀ heteroarylalkyl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group.

According to another aspect, provided is an organic light-emittingdevice including:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes an emission layer, and at least oneorganometallic compound represented by Formula 1.

The emission layer may include the at least one organometallic compound.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with FIG. 1, which is a schematic view of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to the like elements throughout. In this regard, thepresent embodiments may have different forms and should not be construedas being limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the figures, toexplain aspects of the present disclosure. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items). Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

An organometallic compound according to an exemplary embodiment isrepresented by Formula 1:

CY₁ in Formula 1 may be selected from a benzene and a naphthalene.

R₁ to R₃ in Formula 1 may be each independently selected from ahydrogen, a deuterium, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted C₂-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₂-C₆₀ heteroarylthio group, a substituted orunsubstituted C₃-C₆₀ heteroarylalkyl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, and —Si(Q₅₁)(Q₅₂)(Q₅₃)

In some embodiments, R₁ to R₃ in Formula 1 may be each independentlyselected from

a hydrogen, a deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group,and —Si(Q₅₁)(Q₅₂)(Q₅₃),

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, and

Q₅₁ to Q₅₃ may be each independently selected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group.

In some embodiments, R₁ to R₃ in Formula 1 may be each independentlyselected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, a naphthyl group, and —Si(Q₅₁)(Q₅₂)(Q₅₃); and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group,

wherein Q₅₁ to Q₅₃ may be each independently selected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group.

In some embodiments, R₁ to R₃ in Formula 1 may be each independentlyselected from a hydrogen, a deuterium, —CH₃, —CH₂CH₃, —CD₃, —CD₂H,—CDH₂, —CH₂CD₃, and —CD₂CH₃.

In some embodiments, R₁ to R₃ in Formula 1 may be each independentlyselected from —CH₃, —CH₂CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CD₃, and —CD₂CH₃.

In some embodiments, R₁ to R₃ in Formula 1 may be each independentlyselected from a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, groups represented by Formulae 9-1 to 9-19, and groupsrepresented by Formulae 10-1 to 10-18:

* in Formulae 9-1 to 9-19 and 10-1 to 10-18 is a binding site to aneighboring atom.

In some embodiments, R₁ to R₃ in Formula 1 may be each independentlyselected from —CH₃, —CD₃, —CD₂H, —CDH₂, groups represented by Formulae9-1 to 9-19, and a phenyl group, but it may be considered that they arenot limited thereto.

In Formula 1,

R₁ to R₃ may all be identical to each other;

R₁ and R₃ may be identical to each other and R₂ and R₁ may be differentfrom each other; or

R₁ to R₃ may all be different from each other.

In some embodiments, R₁ to R₃ in Formula 1 may all be identical to eachother.

For example, in Formula 1,

R₁ to R₃ may all be identical to each other, and

R₁ to R₃ may be selected from —CH₃, —CD₃, —CD₂H, —CDH₂, groupsrepresented by Formulae 9-1 to 9-19, and a phenyl group, but it may beconsidered that they are not limited thereto.

R₁₁ to R₁₃ and R₂₁ in Formula 1 may be each independently selected froma hydrogen, a cyano group, a deuterium, —F, —Cl, —Br, —I, —SF₅, ahydroxyl group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₇-C₆₀ arylalkylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted C₂-C₆₀ heteroaryloxy group, a substitutedor unsubstituted C₂-C₆₀ heteroarylthio group, a substituted orunsubstituted C₃-C₆₀ heteroarylalkyl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —B(Q₃)(Q₄), and —P(═O)(Q₅)(Q₆),provided that at least one selected from R₁₁ to R₁₃ in Formula 1 may notbe a hydrogen.

In some embodiments, R₁₁ to R₁₃ and R₂₁ in Formula 1 may be eachindependently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, —SF₅, C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; and

—B(Q₃)(Q₄) and —P(═O)(Q₅)(Q₆),

wherein Q₃ to Q₆ may be each independently selected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group, providedthat at least one selected from R₁₁ to R₁₃ in Formula 1 is not ahydrogen.

In some embodiments, R₁₁ to R₁₃ and R₂₁ in Formula 1 may be eachindependently selected from

a hydrogen, a deuterium, —F, a cyano group, a nitro group, —SF₅, amethyl group, an ethyl group, an n-propyl group, an isopropyl group, ann-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentylgroup, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, atert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptylgroup, a tert-heptyl group, an n-octyl group, an iso-octyl group, asec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonylgroup, a sec-nonyl group, a tert-nonyl group, an n-decyl group, anisodecyl group, a sec-decyl group, a tert-decyl group, a methoxy group,an ethoxy group, a propoxy group, butoxy group, a pentoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group,a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an isopentyl group, a sec-pentyl group, atert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexylgroup, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, asec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octylgroup, a sec-octyl group, a tert-octyl group, an n-nonyl group, aniso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decylgroup, an isodecyl group, a sec-decyl group, a tert-decyl group, amethoxy group, an ethoxy group, a propoxy group, butoxy group, a pentoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a cyanogroup, a nitro group, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group,a dibenzofuranyl group, and a dibenzothiophenyl group; and

—B(Q₃)(Q₄) and —P(═O)(Q₅)(Q₆),

wherein Q₃ to Q₆ may be each independently selected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group, providedthat at least one selected from R₁₁ to R₁₃ in Formula 1 may not be ahydrogen.

In some embodiments, R₁₁ to R₁₃ and R₂₁ in Formula 1 may be eachindependently selected from a hydrogen, a deuterium, —F, a cyano group,a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂,groups represented by Formulae 9-1 to 9-19, and groups represented byFormulae 10-1 to 10-36, provided that at least one selected from R₁₁ toR₁₃ in Formula 1 is not a hydrogen:

wherein * in Formulae 9-1 to 9-19 and 10-1 to 10-36 is a binding site toa neighboring atom.

b1 in Formula 1 indicates the number of groups R₂₁. When CY₁ is thebenzene, b1 may be an integer selected from 0 to 4. When CY₁ is thenaphthalene, b1 may be an integer selected from 0 to 6. When b1 is 2 ormore, 2 or more groups R₂₁ may be identical to or different from eachother. For example, b1 may be 0, 1, or 2. In some embodiments, b1 maybe 1. In other embodiments, b1 in Formula 1 may be 0, but it may beconsidered that they are not limited thereto.

In Formula 1,

R₁₁ may not be a hydrogen and R₁₂ and R₁₃ may each be a hydrogen;

R₁₂ may not be a hydrogen and R₁₁ and R₁₃ may each be a hydrogen;

R₁₃ may not be a hydrogen and R₁₁ and R₁₂ may each be a hydrogen;

each of R₁₁ and R₁₂ may not be a hydrogen and R₁₃ may be a hydrogen;

each of R₁₂ and R₁₃ may not be a hydrogen and R₁₁ may be a hydrogen;

each of R₁₁ and R₁₃ may not be a hydrogen and R₁₂ may be a hydrogen; or

each of R₁₁ to R₁₃ may not be a hydrogen at the same time.

In some embodiments, R₁₁ in Formula 1 may not be a hydrogen.

In some embodiments, R₁₁ in Formula 1 may be neither a hydrogen nor amethyl group.

In some embodiments, in Formula 1,

R₁₁ may not be a hydrogen and R₁₂ and R₁₃ may each be a hydrogen; or

R₁₂ may not be a hydrogen and R₁₁ and R₁₃ may be a hydrogen.

For example, R₁₂ in Formula 1 may be a deuterium, —F, —Cl, —Br, —I,—SF₅, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₂₀ alkyl group, a substituted or unsubstituted C₁-C₂₀ alkoxy group,a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₂₀aryl group, a substituted or unsubstituted C₁-C₂₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —B(Q₃)(Q₄), and —P(═O)(Q₅)(Q₆).

In some embodiments, R₁₂ in Formula 1 may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, —SF₅,C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; and

—B(Q₃)(Q₄) and —P(═O)(Q₅)(Q₆),

wherein Q₃ to Q₆ are each independently selected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group.

In some embodiments, R₁₂ in Formula 1 may be a substituted orunsubstituted C₁-C₂₀ alkyl group.

In some embodiments, R₁₂ in Formula 1 may be selected from

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group; and

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group.

In some embodiments, R₁₂ in Formula 1 may be selected from

a C₂-C₂₀ alkyl group and a C₂-C₂₀ alkoxy group;

a methyl group and a methoxy group, each substituted with at least oneselected from C₃-C₆₀ cycloalkyl group, a C₁-C₆₀ heterocycloalkyl group,a C₃-C₆₀ cycloalkenyl group, a C₁-C₆₀ heterocycloalkenyl group, a C₆-C₁₄aryl group, a C₁-C₁₄ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group;

a C₂-C₂₀ alkyl group and a C₂-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₁₄ aryl group, a C₁-C₁₄ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ arylgroup, a C₁-C₁₄ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ arylgroup, a C₁-C₁₄ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group, each substituted with at least one selected froma deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄aryl group, a C₁-C₁₄ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group; and

—B(Q₃)(Q₄) and —P(═O)(Q₅)(Q₆),

wherein Q₃ to Q₆ may be each independently selected from a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₁₄ aryl group, a C₆-C₁₄ aryl groupsubstituted with at least one selected from a C₁-C₂₀ alkyl group and aC₆-C₁₄ aryl group, a C₁-C₁₄ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.

In some embodiments, R₁₂ in Formula 1 may be selected from

a C₂-C₂₀ alkyl group and a C₂-C₂₀ alkoxy group;

a methyl group and a methoxy group, each substituted with at least oneselected from a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a C₂-C₂₀ alkyl group and a C₂-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; and

—B(Q₃)(Q₄) and —P(═O)(Q₅)(Q₆),

wherein Q₃ to Q₆ may be each independently selected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group.

In some embodiments, R₁₂ in Formula 1 may be selected from

an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexylgroup, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, atert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octylgroup, a tert-octyl group, an n-nonyl group, an iso-nonyl group, asec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecylgroup, a sec-decyl group, a tert-decyl group, an ethoxy group, a propoxygroup, butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a pyridinyl group, and a pyrimidinyl group;

a methyl group and a methoxy group, each substituted with at least oneselected from a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group; and

an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexylgroup, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, atert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octylgroup, a tert-octyl group, an n-nonyl group, an iso-nonyl group, asec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecylgroup, a sec-decyl group, a tert-decyl group, an ethoxy group, a propoxygroup, butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a pyridinyl group, and a pyrimidinyl group, each substituted withat least one selected from a deuterium, —F, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a cyano group, a nitro group, a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a pyridinyl group, and a pyrimidinyl group.

In some embodiments, R₁₂ in Formula 1 may be selected from

a C₂-C₂₀ alkyl group;

a methyl group, each substituted with at least one selected from aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄ arylgroup, a C₁-C₁₄ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group; and

a C₂-C₂₀ alkyl group, substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₁₄aryl group, a C₁-C₁₄ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.

In some embodiments, R₁₂ in Formula 1 may be selected from

a C₂-C₂₀ alkyl group;

a methyl group, substituted with at least one selected from acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinylgroup; and

a C₂-C₂₀ alkyl group, substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₁₀ alkyl group, a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinylgroup, but is not limited thereto.

In some embodiments, R₁₂ in Formula 1 may be selected from

an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexylgroup, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, atert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octylgroup, a tert-octyl group, an n-nonyl group, an iso-nonyl group, asec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecylgroup, a sec-decyl group, and a tert-decyl group;

a methyl group, substituted with at least one selected from acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinylgroup; and

an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexylgroup, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, atert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octylgroup, a tert-octyl group, an n-nonyl group, an iso-nonyl group, asec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecylgroup, a sec-decyl group, and a tert-decyl group, each substituted withat least one selected from a deuterium, —F, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a cyano group, a nitro group, a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a pyridinyl group, and a pyrimidinyl group.

R₁₃ in Formula 1 may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; and

—B(Q₃)(Q₄) and —P(═O)(Q₅)(Q₆),

wherein Q₃ to Q₆ may be each independently selected from

a hydrogen, a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H and —CD₂CDH₂;

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and

an n-propyl group, an isopropyl group, an n-butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, anisopentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group, each substituted with at least one selectedfrom a deuterium, a C₁-C₁₀ alkyl group, and a phenyl group, but is notlimited thereto.

For example, the organometallic compound may be represented by one ofFormulae 1-1 to 1-108:

In Formulae 1-1 to 1-108, descriptions of R₁ to R₃ and R₁₁ to R₁₃ arethe same as described above, descriptions of R₁₄ to R₁₇ may beunderstood by referring to descriptions of R₂₁, and descriptions of b1are the same as described above, provided that each of R₁₁ to R₁₇ maynot be a hydrogen.

For example, in Formulae 1-1 to 1-108,

R₁ to R₃ may all be identical to each other,

R₁ to R₃ may be selected from —CH₃, —CD₃, —CD₂H, —CDH₂, groupsrepresented by Formulae 9-1 to 9-19, and a phenyl group,

R₁₁ to R₁₇ and R₂₁ may be each independently selected from a deuterium,—F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, groups represented by Formulae 9-1 to 9-19, and groupsrepresented by Formulae 10-1 to 10-36,

b1 may be 0, 1, or 2, but is not limited thereto.

In some embodiments, the organometallic compound may be represented byone of Formulae 1-1 to 1-48, 1-97 to 1-99 and 1-103 to 1-105, providedthat b1 in Formulae 1-97 to 1-99 and 1-103 to 1-105 is 0.

For example, the organometallic compound may be one of Compounds 1 to96, but is not limited thereto:

At least one selected from R₁₁ to R₁₃ in Formula 1 is not a hydrogen.That is, each of R₁₁ to R₁₃ in Formula 1 may not be a hydrogen at thesame time. In some embodiments, R₁₂ in Formula 1 is not a hydrogen. Insuch conditions, the morphology of the organometallic compoundrepresented by Formula 1 may be improved, and accordingly, a device, forexample, an organic light-emitting device, including the organometalliccompound may have a long lifespan.

In some embodiments, a silyl group (—Si(R₁)(R₂)(R₃)) in Formula 1 (forexample, Formulae 1-1 to 1-108) is bound to a fifth site of a pyridinering, and each of R₁₁ to R₁₇ and R₂₁ is not a silyl group (see Formula 1and Formulae 1-1 to 1-108, and definitions for R₁₁ to R₁₇ and R₂₁). Thatis, a silyl group in Formula 1 may be bound only to a fifth site of apyridine ring. In some embodiments, Formula 1 has identical threeligands. In such conditions, the organometallic compound represented byFormula 1 may have high triplet spin density and thermal stability atthe same time. Accordingly, a device, for example, an organiclight-emitting device, including the organometallic compound representedby Formula 1, may have high efficiency.

For example, some of the organometallic compounds were evaluated byusing a DFT method based on Gaussian program to measure their highestoccupied molecular orbitals (HOMO), lowest unoccupied molecular orbitals(LUMO), and triplet (T₁) energy level (structurally optimized at levelsof B3LYP, 6-31G(d,p)). Evaluation results are shown in Table 1.

TABLE 1 HOMO LUMO T₁ energy level Compound No. (eV) (eV) (eV)  1 −4.714−1.184 2.567  2 −4.718 −1.158 2.572 13 −4.704 −1.120 2.612 32 −4.714−1.184 2.567 Comparative −4.807 −1.205 2.604 material 1

From Table 1, it may be understood that the organometallic compoundrepresented by Formula 1 has a HOMO level and a LUMO level, which aresuitable for an organic light-emitting device, and that theorganometallic compound represented by Formula 1 is a suitable emitterof luminescence energy (T₁) corresponding to visible light region.

Synthesis methods of the organometallic compound represented by Formula1 may be apparent to one of ordinary skill in the art by referring toSynthesis Examples provided below.

The organometallic compound represented by Formula 1 is suitable for usein an organic layer of an organic light-emitting device, for example,for use as a dopant in an emission layer of the organic layer. Thus,another aspect provides an organic light-emitting device that includes:

a first electrode;

a second electrode; and

an organic layer that is disposed between the first electrode and thesecond electrode,

wherein the organic layer includes an emission layer and at least one oforganometallic compound represented by Formula 1.

The organic light-emitting device may have, due to the inclusion of anorganic layer including the organometallic compound represented byFormula 1, low driving voltage, high efficiency, high power, highquantum efficiency, long lifespan and excellent color.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of an organic light-emitting device. For example, theorganometallic compound represented by Formula 1 may be included in theemission layer. In this regard, the organometallic compound may act as adopant, and the emission layer may further include a host (that is, anamount of the organometallic compound represented by Formula 1 issmaller than an amount of the host).

The expression “(an organic layer) includes at least one of theorganometallic compounds” as used herein may include an embodiment inwhich “(an organic layer) includes identical organometallic compounds ofFormula 1 and an embodiment in which (an organic layer) includes two ormore different organometallic compounds of Formula 1.

For example, the organic layer may include, as the organometalliccompound, only Compound 1. In this regard, Compound 1 may be included inan emission layer of the organic light-emitting device. In someembodiments, the organic layer may include, as the organometalliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may be included in an identical layer (for example, Compound1 and Compound 2 may all be included in an emission layer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode; or the first electrode may be a cathode,which is an electron injection electrode, and the second electrode maybe an anode, which is a hole injection electrode.

For example, the first electrode may be an anode, and the secondelectrode may be a cathode, and the organic layer may include:

i) a hole transport region that is disposed between the first electrodeand the emission layer, wherein the hole transport region includes atleast one selected from a hole injection layer, a hole transport layer,and an electron blocking layer, and

ii) an electron transport region that is disposed between the emissionlayer and the second electrode, wherein the electron transport regionincludes at least one selected from a hole blocking layer, an electrontransport layer, and an electron injection layer.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode of an organic light-emitting device. The “organiclayer” may include, in addition to an organic compound, anorganometallic complex including a metal.

FIG. 1 is a schematic view of an organic light-emitting according to anembodiment. Hereinafter, the structure of an organic light-emittingdevice according to an embodiment and a method of manufacturing anorganic light-emitting device according to an embodiment will bedescribed in connection with FIG. 1. The organic light-emitting device10 includes a first electrode 11, an organic layer 15, and a secondelectrode 19, which are sequentially stacked.

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 11 or above the second electrode 19. For use as the substrate,any substrate that is suitable for general organic light-emittingdevices may be used, and the substrate may be a glass substrate ortransparent plastic substrate, each with excellent mechanical strength,thermal stability, transparency, surface smoothness, ease of handling,and water-resistance.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming the first electrode on the substrate. The firstelectrode 11 may be an anode. The material for the first electrode 11may be selected from materials with a high work function to allow holesto be easily provided. The first electrode 11 may be a reflectiveelectrode or a transmissive electrode. The material for the firstelectrode may be, for example, indium tin oxide (ITO), indium zinc oxide(IZO), tin oxide (SnO₂), and zinc oxide (ZnO). In some embodiments,magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as thematerial for the first electrode.

The first electrode 11 may have a single-layer structure or amulti-layer structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 110 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include at least one selected from a holeinjection layer, a hole transport layer, an electron blocking layer, anda buffer layer.

The hole transport region may include only either a hole injection layeror a hole transport layer. In some embodiments, the hole transportregion may have a structure of hole injection layer/hole transport layeror hole injection layer/hole transport layer/electron blocking layer,which are sequentially stacked in this stated order from the firstelectrode 11.

A hole injection layer may be formed on the first electrode 11 by usingvarious methods, such as vacuum deposition, spin coating, casting, orLangmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a material that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100 to about500° C., a vacuum degree of about 10⁻⁸ to about 10⁻³ torr, and adeposition rate of about 0.01 to about 100 Angstroms per second (Å/sec).However, the deposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coatingconditions may vary according to the material used to form the holeinjection layer, and the structure and thermal properties of the holeinjection layer. For example, a coating speed may be from about 2,000revolutions per minute (rpm) to about 5,000 rpm, and a temperature atwhich a heat treatment is performed to remove a solvent after coatingmay be from about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blockinglayer may be understood by referring to conditions for forming the holeinjection layer. The hole transport region may include at least oneselected from m-MTDATA, TDATA, 2-TNATA, NPB, 8-NPB, TPD, Spiro-TPD,Spiro-NPB, methylated NPB, TAPC, HMTPD,4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (Pani/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

Ar₁₀₁ to Ar₁₀₂ in Formula 201 may be each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroarylgroup, a C₂-C₆₀ heteroaryloxy group, a C₂-C₆₀ heteroarylthio group, aC₃-C₆₀ heteroarylalkyl group, a monovalent non-aromatic condensedpolycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.

In Formula 201, xa and xb may be each independently an integer of 0 to5, or 0, 1, or 2. For example, xa is 1 and xb is 0, but xa and xb arenot limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉ and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 maybe each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group (for example, a methyl group, an ethylgroup, a propyl group, a butyl group, a pantyl group, a hexyl group, andso on), and a C₁-C₁₀ alkoxy group (for example, a methoxy group, anethoxy group, a propoxy group, a butoxy group, a pentoxy group, and soon);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group, but it may beconsidered that they are not limited thereto.

R₁₀₉ in Formula 201 may be selected from

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthracenyl group, and a pyridinyl group.

According to an embodiment, the compound represented by Formula 201 maybe represented by Formula 201A, but is not limited thereto:

R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₀ in Formula 201A may be understood byreferring to the description provided herein.

For example, the compound represented by Formula 201, and the compoundrepresented by Formula 202 may include compounds HT1 to HT20 illustratedbelow, but are not limited thereto.

A thickness of the hole transport region may be in a range of about 100Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000Å. While not wishing to be bound by theory, it is understood that whenthe hole transport region includes a hole injection layer and a holetransport layer, the thickness of the hole injection layer may be in arange of about 100 Å to about 10,000 Å, and for example, about 100 Å toabout 1,000 Å, and the thickness of the hole transport layer may be in arange of about 50 Å to about 2,000 Å, and for example, about 100 Å toabout 1,500 Å. While not wishing to be bound by theory, it is understoodthat when the thicknesses of the hole transport region, the holeinjection layer, and the hole transport layer are within these ranges,satisfactory hole transporting characteristics may be obtained without asubstantial increase in driving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments are not limitedthereto. Non-limiting examples of the p-dopant are a quinone derivative,such as tetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenium oxide; and acyano group-containing compound, such as Compound HT-D1 below, but arenot limited thereto.

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer, andthus, efficiency of a formed organic light-emitting device may beimproved.

Then, an emission layer (EML) may be formed on the hole transport regionby vacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied toform the hole injection layer, although the deposition or coatingconditions may vary according to the material that is used to form theemission layer.

Meanwhile, when the hole transport region includes an electron blockinglayer, a material for the electron blocking layer may be selected frommaterials for the hole transport region described above and materialsfor a host to be explained later. However, the material for the electronblocking layer is not limited thereto. For example, when the holetransport region includes an electron blocking layer, a material for theelectron blocking layer may be mCP, which will be explained later.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1.

The host may include at least one selected from TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, TCP, Mcp, Compound HSO, and CompoundH51:

In some embodiments, the host may further include a compound representedby Formula 301 below.

Ar₁₁₁ to Ar₁₁₂ in Formula 301 may be each independently selected from

a phenylene group, a naphthylene group, a phenanthrenylene group, and apyrenylene group; and

a phenylene group, a naphthylene group, a phenanthrenylene group, and apyrenylene group, each substituted with at least one selected from aphenyl group, a naphthyl group, and an anthracenyl group.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may be each independently selected from

a C₁-C₁₀ alkyl group, a phenyl group, a naphthyl group, a phenanthrenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenylgroup, each substituted with at least one selected from a phenyl group,a naphthyl group, and an anthracenyl group.

g, h, l, and j in Formula 301 may be each independently an integer of 0to 4, for example, an integer of 0, 1, or 2.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may be each independently selected from

a C₁-C₁₀ alkyl group substituted with at least one selected from aphenyl group, a naphthyl group, and an anthracenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl, aphenanthrenyl group, and a fluorenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group,a phenanthrenyl group, and a fluorenyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthylgroup, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, anda fluorenyl group; and

but embodiments are not limited thereto.

In some embodiments, the host may include a compound represented byFormula 302 below:

Ar₁₂₂ to Ar₁₂₅ in Formula 302 are the same as described in detail inconnection with Ar₁₁₃ in Formula 301.

Ar₁₂₆ and Ar₁₂₇ in Formula 302 may be each independently a C₁-C₁₀ alkylgroup (for example, a methyl group, an ethyl group, or a propyl group).

k and l in Formula 302 may be each independently an integer of 0 to 4.For example, k and l may be each independently 0, 1, or 2.

The compound represented by Formula 301 and the compound represented byFormula 302 may include Compounds H1 to H42 illustrated below, but arenot limited thereto.

When the organic light-emitting device is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Insome embodiments, due to a stack structure including a red emissionlayer, a green emission layer, and/or a blue emission layer, theemission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 to about 15 parts by weight basedon 100 parts by weight of the host, but is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the emission layer is within this range, excellent light-emissioncharacteristics may be obtained without a substantial increase indriving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer.

For example, the electron transport region may have a structure of holeblocking layer/electron transport layer/electron injection layer or astructure of electron transport layer/electron injection layer, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layer structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, at least one of BCP,Bphen, and BAlq but is not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the hole blocking layer is within these ranges, the hole blockinglayer may have improved hole blocking ability without a substantialincrease in driving voltage.

The electron transport layer may further include at least one selectedfrom BCP, Bphen, Alq₃, BAlq, TAZ, and NTAZ.

In some embodiments, the electron transport layer may include at leastone of ET1 and ET2, but are not limited thereto:

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whilenot wishing to be bound by theory, it is understood that when thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport region may include an electron injection layer(EIL) that promotes flow of electrons from the second electrode 19thereinto.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the electron injection layer is within the range described above, theelectron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be selected from metal, an alloy, an electricallyconductive compound, and a combination thereof, which have a relativelylow work function. For example, lithium (Li), magnesium (Mg), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),or magnesium-silver (Mg—Ag) may be used as a material for forming thesecond electrode 19. In some embodiments, to manufacture a top emissiontype light-emitting device, a transmissive electrode formed using ITO orIZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but is not limited thereto.

A C₁-C₆₀ alkyl group as used herein refers to a linear or branchedaliphatic saturated hydrocarbon monovalent group having 1 to 60 carbonatoms. Detailed examples thereof are a methyl group, an ethyl group, apropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,a pentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkylenegroup as used herein refers to a divalent group having the samestructure as the C₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group as used herein refers to a monovalent grouprepresented by OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group). Detailedexamples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group as used herein refers to a hydrocarbon groupformed by including at least one carbon-carbon double bond in the middleor at the terminal of the C₂-C₆₀ alkyl group. Detailed examples thereofare an ethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group as used herein refers to a hydrocarbon groupformed by including at least one carbon-carbon triple bond in the middleor at the terminal of the C₂-C₆₀ alkyl group. Detailed examples thereofare an ethynyl group, and a propynyl group. A C₂-C₆₀ alkynylene group asused herein refers to a divalent group having the same structure as theC₂-C₆₀ alkynyl group.

A C₃-C₁₀ cycloalkyl group as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms.Detailed examples thereof are a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group as used herein refers to a divalent group having thesame structure as the C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group as used herein refers to a monovalentmonocyclic group having at least one hetero atom selected from N, O, P,and S as a ring-forming atom and 1 to 10 carbon atoms. Detailed examplesthereof are a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.A C₁-C₁₀ heterocycloalkylene group as used herein refers to a divalentgroup having the same structure as the C₁-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group as used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least onecarbon-carbon double bond in the ring thereof, and which not aromatic.Detailed examples thereof are a cyclopentenyl group, a cyclohexenylgroup, and a cycloheptenyl group. A C₃-C₁₀ cycloalkenylene group as usedherein refers to a divalent group having the same structure as theC₃-C₁₀ cycloalkenyl group.

A C₁-C₁₀ heterocycloalkenyl group as used herein refers to a monovalentmonocyclic group that has at least one hetero atom selected from N, O,P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least onedouble bond in its ring. Detailed examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylene group asused herein refers to a divalent group having the same structure as theC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group as used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group as used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group as used herein refers to a monovalent grouphaving an aromatic system that has at least one hetero atom selectedfrom N, O, P, and S as a ring-forming atom, and 1 to 60 carbon atoms. AC₁-C₆₀ heteroarylene group as used herein refers to a divalent grouphaving a carbocyclic aromatic system that has at least one hetero atomselected from N, O, P, and S as a ring-forming atom, and 1 to 60 carbonatoms. Examples of the C₁-C₆₀ heteroaryl group are a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀ heteroarylene group each include two ormore rings, the rings may be fused to each other.

A C₆-C₆₀ aryloxy group as used herein indicates —OA₁₀₂ (wherein A₁₀₂ isthe C₆-C₆₀ aryl group), a C₆-C₆₀ arylthio group as used herein indicates—SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group), and a C₇-C₆₀ arylalkylgroup as used herein indicates -A₁₀₄A₁₀₅ (wherein A₁₀₄ is the C₆-C₅₉aryl group and A₁₀₅ is the C₁-C₅₃ alkyl group).

A C₂-C₆₀ heteroaryloxy group as used herein indicates —OA₁₀₆ (whereinA₁₀₆ is the C₂-C₆₀ heteroaryl group), a C₂-C₆₀ heteroarylthio group asused herein indicates —SA₁₀₇ (wherein A₁₀₇ is the C₂-C₆₀ heteroarylgroup), and a C₃-C₆₀ heteroarylalkyl group as used herein indicates-A₁₀₈A₁₀₉ (wherein A₁₀₈ is the C₂-C₅₉ heteroaryl group and A₁₀₉ is theC₁-C₅₈ alkyl group).

A monovalent non-aromatic condensed polycyclic group as used hereinrefers to a monovalent group (for example, having 8 to 60 carbon atoms)that has two or more rings condensed to each other, only carbon atoms asa ring forming atom, and which is non-aromatic in the entire molecularstructure. A detailed example of the monovalent non-aromatic condensedpolycyclic group is a fluorenyl group. A divalent non-aromatic condensedpolycyclic group as used herein refers to a divalent group having thesame structure as the monovalent non-aromatic condensed polycyclicgroup.

A monovalent non-aromatic condensed heteropolycyclic group as usedherein refers to a monovalent group (for example, having 2 to 60 carbonatoms) that has two or more rings condensed to each other, has aheteroatom selected from N, O, P, and S, other than carbon atoms, as aring forming atom, and which is non-aromatic in the entire molecularstructure. An example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. A divalent non-aromaticcondensed heteropolycyclic group as used herein refers to a divalentgroup having the same structure as the monovalent non-aromatic condensedheteropolycyclic group.

At least one of substituents of the substituted C₁-C₆₀ alkyl group,substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynyl group,substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkyl group,substituted C₁-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₁-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₇-C₆₀ arylalkyl group,substituted C₁-C₆₀ heteroaryl group, substituted C₂-C₆₀ heteroaryloxygroup, substituted C₂-C₆₀ heteroarylthio group, substituted C₃-C₆₀heteroarylalkyl group, substituted monovalent non-aromatic condensedpolycyclic group and substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroarylgroup, a C₂-C₆₀ heteroaryloxy group, a C₂-C₆₀ heteroarylthio group, aC₃-C₆₀ heteroarylalkyl group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, —N(Q₁₁)(Q₁₂), —B(Q₁₃)(Q₁₄), and —P(═O)(Q₁₅)(Q₁₆),

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ heteroaryloxygroup, a C₂-C₆₀ heteroarylthio group, a C₃-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ heteroaryloxygroup, a C₂-C₆₀ heteroarylthio group, a C₃-C₆₀ heteroarylalkyl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₇-C₆₀ arylalkyl group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀ heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₂₁)(Q₂₂), —B(Q₂₃)(Q₂₄), and —P(═O)(Q₂₅)(Q₂₆); and

—N(Q₃₁)(Q₃₂), —B(Q₃₃)(Q₃₄), and —P(═O)(Q₃₅)(Q₃₆);

wherein Q₁ to Q₆, Q₁₁ to Q₁₆, Q₂₁ to Q₂₆, Q₃₁ to Q₃₆ and Q₅₁ to Q₅₃ maybe each independently selected from a hydrogen, a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a C₇-C₆₀ arylalkyl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a C₂-C₆₀ heteroaryloxy group, aC₂-C₆₀ heteroarylthio group, a C₃-C₆₀ heteroarylalkyl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group.

When a group containing a specified number of carbon atoms issubstituted with any of the groups listed in the preceding paragraph,the number of carbon atoms in the resulting “substituted” group isdefined as the sum of the carbon atoms contained in the original(unsubstituted) group and the carbon atoms (if any) contained in thesubstituent. For example, when the term “substituted C₁-C₆₀ alkyl”refers to a C₁-C₆₀ alkyl group substituted with C₆-C₆₀ aryl group, thetotal number of carbon atoms in the resulting aryl substituted alkylgroup is C₇-C₁₂₀.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the organic light-emitting device is notlimited thereto. The wording “B was used instead of A” used indescribing Synthesis Examples means that an amount of A used wasidentical to an amount of B used, in terms of a molar equivalent.

EXAMPLE Synthesis Example 1: Synthesis of Compound 1

50 milliliters (mL) of 2-ethoxyethanol was mixed with Compound A (5.23grams (g), 21.7 millimoles (mmol)) and Ir(COD)₂BF₄ (3.25 g, 6.6 mmol),and the mixture was stirred at a temperature of 120° C. for 18 hours tocarry out a reaction. The resulting was cooled and filtered to obtain asolid, which was then subjected to column chromatography using methylenechloride (MC) and hexane, thereby obtaining 1.9 g (32%) of Compound 1.The identity of the obtained compound was confirmed by Mass and HPLCanalysis.

HRMS (MALDI) calcd for C₄₅H₅₄IrN₃Si₃: m/z 913.3255. Found: 913.3251.

Synthesis Example 2: Synthesis of Compound 2

1.1 g (18%) of Compound 2 was obtained in the same manner as Compound 1in Synthesis Example 1, except that Compound B (5.23 g, 21.7 mmol) wasused instead of Compound A.

HRMS (MALDI) calcd for C₄₅H₅₄IrN₃Si₃: m/z 913.3255. Found: 913.3257.

Synthesis Example 3: Synthesis of Compound 13

2.2 g (37%) of Compound 13 was obtained in the same manner as Compound 1in Synthesis Example 1, except that Compound C (5.40 g, 19.1 mmol) wasused instead of Compound A.

HRMS(MALDI) calcd for C₅₄H₇₂IrN₃Si₃: m/z 1039.4663. Found: 1039.4660.

Synthesis Example 4: Synthesis of Compound 21

2.2 g (37%) of Compound 21 was obtained in the same manner as Compound 1in Synthesis Example 1, except that Compound D (5.40 g, 19.1 mmol) wasused instead of Compound A.

HRMS (MALDI) calcd for C₅₇H₇₂IrN₃Si₃: m/z 1075.4663. Found: 1075.4666.

Synthesis Example 5: Synthesis of Compound 32

2.5 g (42%) of Compound 32 was obtained in the same manner as Compound 1in Synthesis Example 1, except that Compound E (5.27 g, 21.4 mmol) wasused instead of Compound A.

HRMS (MALDI) calcd for C₄₅H₄₅D₉IrN₃Si₃: m/z 922.3820. Found: 922.2817.

Synthesis Example 6: Synthesis of Compound 44

1.3 g (22%) of Compound 44 was obtained in the same manner as Compound 1in Synthesis Example 1, except that Compound F (5.35 g, 19.9 mmol) wasused instead of Compound A.

HRMS (MALDI) calcd for C₅₁H₆₆IrN₃Si₃: m/z 997.4194. Found: 997.4191.

Synthesis Example 7: Synthesis of Compound 91

1.2 g (20%) of Compound 91 was obtained in the same manner as Compound 1in Synthesis Example 1, except that Compound G (5.62 g, 15.6 mmol) wasused instead of Compound A.

HRMS (MALDI) calcd for C₇₂H₈₄IrN₃Si₃: m/z 1267.5602. Found: 1267.5607.

Comparative Synthesis Example 1: Synthesis of Comparative Material 1Synthesis of Compound M2

210 mL of ethoxyethanol and 70 mL of distilled water were mixed with2-phenylpyridine (14.66 g, 94.44 mmol) and iridium chloride (14.8 g,41.97 mmol), and the mixture was stirred for 24 hours under reflux tocarry out a reaction, and cooled to room temperature, thereby generatinga solid. The solid was separated by filtration, and thoroughly,sequentially washed with water, methanol, and hexane in the statedorder. The resultant solid was dried in a vacuum oven to obtain 20.2 g(90%) of Compound M2.

Synthesis of Compound M1

60 mL of MC was mixed with Compound M2 (4.5 g, 4.20 mmol), and AgOTf(2.16 g, 8.41 mmol) dissolved in 20 mL of methanol was added thereto.Thereafter, while light was blocked by using an aluminum foil, theresultant mixture was stirred at room temperature for 18 hours to carryout a reaction, and the solid generated therefrom was removed by celitefiltration. A filtrate was subjected to reduced pressure to obtain asolid (Compound M1), which was used in the following reaction withoutadditional purification.

Synthesis of Comparative Material 1

Compound M1 (6 g, 8.41 mmol) and Compound A (3.0 g, 12.61 mmol) weremixed with 90 mL of ethanol, and the mixture was stirred for 18 hoursunder reflux to carry out a reaction. The temperature was subsequentlyreduced. The resultant mixture was filtered to obtain a solid, which wasthen thoroughly washed with ethanol and hexane. The resulting solid wassubjected to column chromatography using MC and hexane, therebyobtaining 2.1 g (38%) of Comparative material 1. The identity of theobtained compound was confirmed by Mass and HPLC analysis.

Example 1

An ITO glass substrate was cut to a size of 50 millimeters (mm)×50mm×0.5 mm, and sonicated in acetone isopropyl alcohol and pure water,each for 15 minutes, and subsequently washed by exposure to UV ozone for30 minutes.

Then, m-MTDATA was deposited on an ITO electrode (anode) on the glasssubstrate at a deposition speed of 1 Å/sec to form a hole injectionlayer having a thickness of 600 Å, and α-NPD was deposited on the holeinjection layer at a deposition speed of 1 Å/sec to form a holetransport layer having a thickness of 250 Å.

Compound 1 (dopant) and CBP (host) were co-deposited on the holetransport layer at deposition speeds of 0.1 Å/sec and 1 Å/sec,respectively, to form an emission layer having a thickness of 400 Å.

BAlq was deposited on the emission layer at a deposition speed of 1Å/sec to form a hole blocking layer having a thickness of 50 Å, and Alq₃was deposited on the hole blocking layer to form an electron transportlayer having a thickness of 300 Å. Subsequently, LiF was deposited onthe electron transport layer to form an electron injection layer havinga thickness of 10 Å, and Al was vacuum-deposited on the electroninjection layer to form a second electrode(cathode) having a thicknessof 1,200 Å, thereby completing manufacture of an organic light-emittingdevice having the structure of ITO/m-MTDATA (600 Å)/α-NPD (250Å)/CBP+10% (Compound 1) (400 Å)/BAlq (50 Å)/Alq3 (300 Å)/LiF(10 Å)/Al(1,200 Å).

Examples 2 to 7 and Comparative Example 1

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that in forming an emission layer, compounds shownin Table 2 were used instead of Compound 1, as a dopant.

Evaluation Example 1: Evaluation on Characteristics of OrganicLight-Emitting Device

The organic light-emitting devices manufactured according to Examples 1to 7 and Comparative Example 1 were evaluated in terms of drivingvoltage, efficiency, power, color purity, quantum efficiency, andlifespan (T₉₅). Results thereof are shown in Table 2. This evaluationwas performed using a current-voltage meter (Keithley 2400) and abrightness meter (Minolta Cs-1000A), and the lifespan (T₉₅) (at 6,000nit) was evaluated by measuring the amount of time that elapsed untilbrightness was reduced to 95% of the initial brightness of 100%.

TABLE 2 Driving Quantum Lifespan voltage Efficiency Power efficiency(hr) Dopant (V) (cd/A) (Im/W) CIEx CIEy (%) (T₉₅) Example 1 Compound 15.4 54.4 31.6 0.332 0.668 18 175 Example 2 Compound 2 5.2 51.0 30.80.360 0.594 18 195 Example 3 Compound 5.3 56.9 33.7 0.328 0.671 19 35013 Example 4 Compound 5.1 58.0 35.7 0.325 0.670 19 315 21 Example 5Compound 5.3 50.3 29.8 0.370 0.665 18 150 32 Example 6 Compound 5.3 50.630.0 0.365 0.670 18 164 44 Example 7 Compound 5.4 53.4 31.1 0.340 0.66819 235 91 Comparative Comparative 5.3 48.5 28.7 0.344 0.604 18 135Example 1 material 1

From Table 2, it can be understood that the organic light-emittingdevices of Examples 1 to 7 had a comparable driving voltage, higherefficiency, higher power, higher color purity, comparable quantumefficiency, and longer lifetime than the organic light-emitting deviceof Comparative Example 1.

Organometallic compounds according to the present embodiments haveexcellent electric characteristics and thermal stability. Accordingly,an organic light-emitting device including such organometallic compoundsmay have excellent driving voltage, current density, efficiency, power,color purity, and lifespan characteristics.

It should be understood that the exemplary embodiments described thereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

What is claimed is:
 1. An organometallic compound represented by one ofFormulae 1-1, 1-3, 1-10, 1-12, and 1-17:

wherein in Formulae 1-1, 1-3, 1-10, 1-12, and 1-17, R₁ to R₃ are eachindependently selected from: —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂; an n-propyl group, an isopropyl group, ann-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,an n-pentyl group, an isopentyl group, a sec-pentyl group, and atert-pentyl group; and an n-propyl group, an isopropyl group, an n-butylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, ann-pentyl group, an isopentyl group, a sec-pentyl group, and atert-pentyl group, each substituted with at least one deuterium, R₁₂ isselected from: a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group,a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, and a phenyl group; and a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an isopentyl group, a sec-pentyl group, a tert-pentyl group, ann-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexylgroup, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, atert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octylgroup, a tert-octyl group, an n-nonyl group, an iso-nonyl group, asec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecylgroup, a sec-decyl group, a tert-decyl group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and aphenyl group, each substituted with at least one selected from adeuterium, —CD₃, —CD₂H, —CDH₂, and a C₁-C₁₀ alkyl group; and R₁₃ isselected from: a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decyl group, an isodecyl group, a sec-decyl group, and a tert-decylgroup; and a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decyl group, an isodecyl group, a sec-decyl group, and a tert-decylgroup, each substituted with at least one deuterium; and R₁₅ is selectedfrom: a deuterium, a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group,and a phenyl group; and a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, an isobutyl group, asec-butyl group, a tert-butyl group, an n-pentyl group, an isopentylgroup, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, aniso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptylgroup, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, ann-octyl group, an iso-octyl group, a sec-octyl group, a tert-octylgroup, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, atert-nonyl group, an n-decyl group, an isodecyl group, a sec-decylgroup, a tert-decyl group, and a phenyl group, each substituted with atleast one selected from a deuterium, —CD₃, —CD₂H, —CDH₂, and a C₁-C₁₀alkyl group; and R₁₆ is a deuterium; and R₁₇ is selected from: adeuterium, a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decyl group, an isodecyl group, a sec-decyl group, and a tert-decylgroup; and a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentylgroup, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decyl group, an isodecyl group, a sec-decyl group, and a tert-decylgroup, each substituted with at least one deuterium.
 2. Theorganometallic compound of claim 1, wherein R₁ to R₃ are eachindependently selected from —CH₃, —CD₃, —CD₂H, —CDH₂, and groupsrepresented by Formulae 9-1 to 9-19:

wherein * in Formulae 9-1 to 9-19 is a binding site to a neighboringatom.
 3. The organometallic compound of claim 1, wherein R₁ to R₃ areall identical to each other, and R₁ to R₃ are selected from —CH₃, —CD₃,—CD₂H, —CDH₂, and groups represented by Formulae 9-1 to 9-19:

wherein * in Formulae 9-1 to 9-19 is a binding site to a neighboringatom.
 4. The organometallic compound of claim 1, wherein R₁₂ is selectedfrom —CH₃, —CD₃, —CD₂H, —CDH₂, and groups represented by Formulae 9-1 to9-19, 10-1 to 10-9, 10-31, 10-32 and 10-36, R₁₃ is selected from —CH₃,—CD₃, —CD₂H, —CDH₂, and groups represented by Formulae 9-1 to 9-19, R₁₅is selected from a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, and groupsrepresented by Formulae 9-1 to 9-19, 10-1 to 10-6, and 10-36, and R₁₇ isselected from a deuterium, —CH₃, —CD₃, —CD₂H, —CDH₂, and groupsrepresented by Formulae 9-1 to 9-19:

wherein * in Formulae 9-1 to 9-19, 10-1 to 10-9, 10-31, 10-32 and 10-36is a binding site to a neighboring atom.
 5. The organometallic compoundof claim 1, wherein R₁ to R₃ are all identical to each other, R₁ to R₃are selected from —CH₃, —CD₃, —CD₂H, —CDH₂, and groups represented byFormulae 9-1 to 9-19, R₁₂ is selected from —CH₃, —CD₃, —CD₂H, —CDH₂, andgroups represented by Formulae 9-1 to 9-19, 10-1 to 10-9, 10-31, 10-32and 10-36, R₁₃ is selected from —CH₃, —CD₃, —CD₂H, —CDH₂, and groupsrepresented by Formulae 9-1 to 9-19, R₁₅ is selected from a deuterium,—CH₃, —CD₃, —CD₂H, —CDH₂, and groups represented by Formulae 9-1 to9-19, 10-1 to 10-6, and 10-36, and R₁₇ is selected from a deuterium,—CH₃, —CD₃, —CD₂H, —CDH₂, and groups represented by Formulae 9-1 to9-19:

wherein * in Formulae 9-1 to 9-19, 10-1 to 10-9, 10-31, 10-32, and 10-36is a binding site to a neighboring atom.
 6. An organic light-emittingdevice comprising: a first electrode; a second electrode; and an organiclayer disposed between the first electrode and the second electrode,wherein the organic layer comprises an emission layer, and at least oneorganometallic compound of claim
 1. 7. The organic light-emitting deviceof claim 6, wherein the emission layer comprises the at least oneorganometallic compound.
 8. An organometallic compound being representedby one of Compounds 1, 2, 4, 5, 7, 8, 10, 11, 13, 14, 16, 17, 19, 20,21, 22, 24, 25, 27, 28, 30, 31, 32, 35, 38, 40, 42, 44, 47, 50, 52, 54,75 to 84, and 91: